# US 11,444,250 B2 · Composition of matter for use in organic light-emitting diodes > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,444,250 B2 - Document ID: US11444250B2 - Status: Granted - Kind: B2 - Application number: 16/210,422 - Filed: 2018-12-05 - Published: 2019-06-06 - Granted: 2022-09-13 - Earliest claimed: 2017-12-05 - Assignees: Kyulux, Inc. - Applicants: Kyulux, Inc. - Inventors: Yoshitake Suzuki; Shuo-Hsien Cheng; Yu Seok Yang; Jorge Aguilera-Iparraguirre; Rafael Gomez-Bombarelli; Timothy D. Hirzel - Web page: https://patentgrep.com/patent/US11444250B2 ## CPC - H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole} - C07D 403/10: linked by a carbon chain containing aromatic rings - C09K 11/06: containing organic luminescent materials - H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)} - C09K 2211/1018: Heterocyclic compounds - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 2101/10: Triplet emission - H10K 2101/30: Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values - H10K 2101/40: Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers - H10K 2102/103: {comprising indium oxides, e.g. ITO} - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE ## Abstract The present disclosure relates to compounds of Formula (I) as compounds capable of emitting delayed fluorescence, and uses of the compounds in organic light-emitting diodes. ## Claims ### Claim 1 A compound of Formula (I): wherein A is selected from CN X1, X2, X3, and X4 are independently selected from H, CN, F, CF3, SO2Ph, SO2Me, and NO2 provided that when A is CN and X2 is F or CF3, then X3 is F, or that when both A and X2 are CN, then X3 is H, F, CF3, SO2Ph, SO2Me, or NO2; at least one instance of X1, X2, X3, and X4 is not H; R1, R2, R3, R4, and R5 are independently selected from H, deuterium, Ph, and D; provided that R2 and R4 are not D; D is independently selected from R11 to R18 and R31 to R38 each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, CN, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, or a substituted or unsubstituted diarylamine; each of R11 and R12, R12 and R13, R13 and R14, R15 and R16, R16 and R17, R17 and R18, L11 and R11, L11 and R18 taken together can form a ring system; each of R31 and R32, R32 and R33, R33 and R34, R35 and R36, R36 and R37, R37 and R38, L13 and R31, L13 and R38 taken together can form a ring system; L11 and L13 each independently represents a single bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene; X represents O, S, a substituted or unsubstituted nitrogen atom, a substituted or unsubstituted carbon atom, a substituted or unsubstituted silicon atom, a carbonyl, a divalent substituted or unsubstituted ethylene having a bonding chain length of 2 atoms, a substituted or unsubstituted vinylene; a substituted or unsubstituted o-arylene, or a substituted or unsubstituted o-heteroarylene; and Y represents C or N, and no more than one instance of Y is N; n is 1; provided that if an instance of Y is N, then the corresponding substituent selected from to R31 to R34 is absent, provided that at least one of the following conditions (a) to (c) is satisfied: (a) A is selected from A1 to A13, and X1, X2, X3, and X4 are independently selected from CN, F, CF3, SO2Ph, SO2Me, and NO2, (b) X1, X2, X3, and X4 are independently selected from H, F, CF3, SO2Ph, SO2Me, and NO2, and at least one instance of R1, R3, and R5 is D, and (c) D is independently D-II, and at least one instance of R1, R3, and R5 is D. ### Claim 2 (depends on 1) The compound of claim 1, wherein D is independently selected from: Z is independently selected from Me, i-propyl, t-Bu, and heteroaryl, and heteroaryl is independently selected from ### Claim 3 (depends on 2) The compound of claim 2, wherein at least one instance of R1, R3, and R5 is D and wherein D is independently selected from D1, D3, D6, D9, D11, D13, D15, D16, D28, D30, D32, D34, D36, and D37. ### Claim 4 (depends on 3) The compound of claim 3, wherein at least one instance of R1, R3, and R5 is D and wherein D is D36 or D37; and Z is H. ### Claim 5 (depends on 3) The compound of claim 3, wherein at least one instance of R1, R3, and R5 is D and wherein D is D36 or D37; and Z is Me, i-propyl, or t-Bu. ### Claim 6 (depends on 3) The compound of claim 3, wherein at least one instance of R1, R3, and R5 is D and wherein D is D36 or D37; and Z is heteroaryl. ### Claim 7 (depends on 2) The compound of claim 2, wherein at least one instance of R1, R3, and R5 is D and wherein D is independently selected from D2, D4 D7, D10, D29, D31, D33, and D35. ### Claim 8 (depends on 2) The compound of claim 2, wherein at least one instance of R1, R3, and R5 is D and wherein D is independently selected from D5, D8, D12, and D14. ### Claim 9 (depends on 2) The compound of claim 2, wherein at least one instance of R1, R3, and R5 is D and wherein D is independently selected from D17, D18, D19 and D20. ### Claim 10 (depends on 2) The compound of claim 2, wherein at least one instance of R1, R3, and R5 is D and wherein D is independently selected from D21, D22 and D23. ### Claim 11 (depends on 2) The compound of claim 2, wherein at least one instance of R1, R3, and R5 is D and wherein D is independently selected from D24, D25, D26, and D27. ### Claim 12 (depends on 1) The compound of claim 1, wherein at least one instance of X1, X2, X3, and X4 is F. ### Claim 13 (depends on 1) The compound of claim 1, wherein all instances of X1, X2, X3, and X4 are F. ### Claim 14 (depends on 1) The compound of claim 1, wherein A is A7, A11, or A12. ### Claim 15 (depends on 1) The compound of claim 1, selected from ### Claim 16 (depends on 1) The compound of claim 1, selected from ### Claim 17 (depends on 1) An organic light-emitting diode (OLED) comprising an anode, a cathode, and at least one organic layer comprising a light emitting layer between the anode and the cathode, wherein the light-emitting layer comprises: a compound of claim 1. ### Claim 18 (depends on 17) The organic light-emitting diode (OLED) of claim 17, wherein the compound is a light emitting material. ### Claim 19 (depends on 17) The organic light-emitting diode (OLED) of claim 17, wherein the compound is capable of emitting delayed fluorescence. ### Claim 20 (depends on 1) The Compound of claim 1, wherein the condition (a) is satisfied. ### Claim 21 (depends on 1) The Compound of claim 1, wherein the condition (b) is satisfied. ### Claim 22 (depends on 1) The Compound of claim 1, wherein the condition (c) is satisfied.